(R)-(+)-2-甲基丁胺 | 36272-22-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(+)-2-甲基丁胺
• 英文名称: (R)-(+)-2-methylbutylamine
• 英文别名: (R)-2-methylbutan-1-amine；(R)-2-methylbutanamine；(R)-2-methylbutylamine；(2R)-2-methylbutan-1-amine
• CAS: 36272-22-7
• 化学式: C₅H₁₃N
• 分子量: 87.1649
• InChiKey: VJROPLWGFCORRM-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-甲基丁胺 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S)-2-amino-4-methyl-N-[(2R)-2-methylbutyl]pentanamide
  参考文献：
  名称：

  Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands

  摘要：

  A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S-2' pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P-2' substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.

  DOI：

  10.1021/acs.jmedchem.6b00998
• 作为产物：
  描述：

  (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-((R)-2-methylbutyl)penta-2,4-dienamide 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (R)-(+)-2-甲基丁胺
  参考文献：
  名称：

  Piper chaba果实中的保肝酰胺成分：结构要求，作用方式和新酰胺

  摘要：

  发现从胡椒木果实中提取的80％丙酮水溶液对小鼠的d-半乳糖胺（d -GalN）/脂多糖诱导的肝损伤具有保肝作用。从可溶于乙酸乙酯的馏分中，分离出三种新的酰胺，哌甲酰胺E，G和H，33种酰胺和四种芳族成分。在分离物中，几种酰胺成分可抑制d-GalN /肿瘤坏死因子-α（TNF-α）诱导的肝细胞死亡，并提出以下结构要求：（i）酰胺部分对于有效活性至关重要；（ii）苯环和酰胺部分之​​间的1，9-癸二烯结构倾向于增强活性。此外，主要成分胡椒碱在口服剂量为5和10 mg / kg时表现出强大的体内保肝作用，其作用方式被认为取决于肝细胞对TNF-α敏感性的降低。

  DOI：

  10.1016/j.bmc.2009.08.050

文献信息

• Synthesis of Chiral Amines via a Bi‐Enzymatic Cascade Using an Ene‐Reductase and Amine Dehydrogenase
  作者：Ewald P. J. Jongkind、Aurélie Fossey‐Jouenne、Ombeline Mayol、Anne Zaparucha、Carine Vergne‐Vaxelaire、Caroline E. Paul

  DOI：10.1002/cctc.202101576

  日期：2022.1.21

  Dynamic duo: The combination of Old Yellow Enzymes and amine dehydrogenases gives access to chiral amines. By combining these enzymes with a cofactor recycling system into a cascade, inexpensive unsaturated aldehydes and ketones were converted into chiral amines with up to two stereocenters and high enantiopurity.

  动态二重奏：旧黄色酶和胺脱氢酶的组合可以使用手性胺。通过将这些酶与辅因子回收系统组合成级联，廉价的不饱和醛和酮被转化为具有多达两个立体中心和高对映纯度的手性胺。
• Psammocindoles A–C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge <i>Psammocinia vermis</i>
  作者：Oh-Seok Kwon、Sungjin Ahn、Ju-eun Jeon、In Guk Park、Tae Hyung Won、Chung J. Sim、Hyeung-geun Park、Dong-Chan Oh、Ki-Bong Oh、Minsoo Noh、Jongheon Shin

  DOI：10.1021/acs.orglett.1c01410

  日期：2021.6.18

  Psammocindoles A–C (1–3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A–D (5–8) were also synthesized. These natural products

  Psammocindoles A–C ( 1 – 3 ) 是一类新的吲哚生物碱，是从Psammocinia vermis海绵中分离出来的。通过组合光谱分析，这些化合物的结构被确定为来自三个氨基酸残基的吲哚-γ-内酰胺。此外，还合成了对映异构体 psammocindole D ( 4 ) 和N-内酰胺异构体 isopsammocindole A–D ( 5 – 8 )。发现这些天然产物和合成类似物可显着刺激人骨髓间充质干细胞中的脂联素分泌。
• Simple Protocol for NMR Analysis of the Enantiomeric Purity of Primary Amines
  作者：Yolanda Pérez-Fuertes、Andrew M. Kelly、Andrew L. Johnson、Susumu Arimori、Steven D. Bull、Tony D. James

  DOI：10.1021/ol052776g

  日期：2006.2.1

  [reaction: see text] A practically simple three-component chiral derivatizing protocol for determining the enantiopurity of 13 chiral primary amines by (1)H NMR spectroscopic analysis is described, including analysis of those that contain remote stereocenters.

  [反应：见正文]描述了一种通过（1）H NMR光谱分析来确定13种手性伯胺的对映体纯度的实用简单的三组分手性衍生化方案，包括对那些包含远程立体中心的分析。
• Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp
  作者：Toru Tachihara、Susumu Ishizaki、Yoshiko Kurobayashi、Hiroshi Tamura、Youichi Ikemoto、Atsushi Onuma、Keisuke Yoshikawa、Tetsuya Yanai、Takeshi Kitahara

  DOI：10.1002/hlca.200390028

  日期：2003.2

  All possible stereoisomers of imine derivatives 1–4, which have the characteristic roast odor of seafood, were synthesized. As a result of odor evaluation of all isomers, we found that each isomer has a different and characteristic odor of roasted seafood.

  亚胺衍生物的所有可能的立体异构1 - 4，其具有海鲜的特性烤气味，合成。通过对所有异构体进行气味评估的结果，我们发现每种异构体具有不同的烧烤海鲜特征气味。
• SYNTHESIS OF THE FOUR POSSIBLE STEREOISOMERS OF<i>N</i>-2′-METHYLBUTYL-2-METHYLBUTYLAMIDE, THE SEX PHEROMONE OF THE LONGHORN BEETLE<i>MIGDOLUS FRYANUS</i>WESTWOOD
  作者：Ellen M. Santangelo、Paulo H. G. Zarbin、Quezia B. Cass、José T. B. Ferreira、Arlene G. Corrêa

  DOI：10.1081/scc-100107019

  日期：2001.1

  four stereoisomers of N-2′-methylbutyl-2-methylbutylamide, the sex pheromone of the longhorn beetle Migdolus fryanus, an economically important pest of sugarcane in South America, were synthesized. The key intermediate 2-methylbutan-1-ol is commercially available only in its (S)-(−)-form. The (R)-(+)-enantiomer was obtained optically pure from methyl (S)-(+)-3-hydroxy-2-methylpropionate in five steps

  合成了N-2'-甲基丁基-2-甲基丁基酰胺的四种立体异构体，它是南美洲重要的甘蔗害虫Migdolus furyanus 的性信息素。关键中间体 2-methylbutan-1-ol 仅以其 (S)-(-)-形式在市场上销售。(R)-(+)-对映异构体分五步从(S)-(+)-3-羟基-2-甲基丙酸甲酯获得光学纯的。